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Why Listen:
I just wrapped up my conversation with Shawn, and it was so enjoyable. There were a couple of things that stood out to me. One was his great quote about always being ready for opportunities and embracing the right thing. His story is so incredible, from this perspective, starting with his unexpected medical discharge from the military, to a winding road through consulting and startups, and ultimately back to startups and starting his own company. It just really shows you the power of resilience, but also the power of being open to unexpected deviations in your career, which will inevitably happen.
Second of all, we talk a lot about networking. He gives a couple of really poignant examples where 10 to 20 years after meeting someone, he and people in his network, reconnect in a way that alters their career. It really gets away from this transactional thought of networking and moves toward something that veterans excel at, which is genuinely meeting people, enjoying them, and being generous.
To that point, immediately after recording, Shawn asked me, “How can I help you with your company Captivate.ai?” It was just so powerful to see him immediately and genuinely putting to use his principle - approaching networking from a generous and giving standpoint.
We talk about grad school, he gives an example of a friend who sold his company for $240 million and then went to business school. He underscores this thought by showing that there is no “one right size fits all” approach to education and your career journey. It's about learning and serendipity.
Finally, we talk about his own startup journey and the milestones achieved along the way as he created and continues to build his company. I did something for the first time in this interview, which is a kind of live mentorship where I asked him a specific question about my company Captivate.ai. I think his answer will benefit anyone interested in entrepreneurship.
About Shawn:
Shawn Olds is the Co-Founder and Chief Executive Officer at boodleAI, which specializes in Enriched Analytics for sales, marketing and fundraising teams. boodleAI is on a mission to democratize data, making it faster and easier for ALL organizations to locate their best leads and prospects in any contact list. By using advanced data enrichment and predictive insight analytics, boodleAI clients have already experienced significant lifts in conversion, engagement, and retention rates. boodleAI has over 30 employees, has raised $3M in funding, and is located in Tysons, VA. Shawn holds a B.S. from West Point, an MBA from Northwestern's Kellogg School of Management, and a JD from Northwestern's Pritzker School of Law.
Selected Resources:
Shawn’s LinkedIn - https://www.linkedin.com/in/shawnnolds
boodleAI - https://boodle.ai/
Time Stamps:
Shawn’s background [0:40]
From consulting to starting boodleAI [6:45]
When it’s best for Veterans to go back to school [12:27]
BoodleAI and Shawn’s role as Co-founder and CEO [18:17]
How Shawn views milestones in a company [25:47]
When should you consider fundraising or investing? [29:51]
Shawn advice on networking [39:19]